Dimethylformamide → 2-(3-{(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro[1,2,4]triazol-1-yl)benzoic acid

HRID 1161574Notes

Reaction equation

HRID 1161574 reaction equation
CN(C=O)C.CO[C:8](=[O:39])[N:9]=[C:10](SC)[C:11]([C:25]1[CH:26]=[C:27]([O:35][CH3:36])[C:28]2[O:33][CH2:32][O:31][CH2:30][C:29]=2[CH:34]=1)=[N:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]=[C:22]([CH3:24])[O:21][N:20]=2)=[CH:15][CH:14]=1.Cl.[NH:41]([C:43]1[CH:51]=[CH:50][CH:49]=[CH:48][C:44]=1[C:45]([OH:47])=[O:46])[NH2:42]>C(N(CC)CC)C>[CH3:36][O:35][C:27]1[C:28]2[O:33][CH2:32][O:31][CH2:30][C:29]=2[CH:34]=[C:25]([CH:11]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[N:23]=[C:22]([CH3:24])[O:21][N:20]=3)=[CH:17][CH:18]=2)[C:10]2[NH:9][C:8](=[O:39])[N:41]([C:43]3[CH:51]=[CH:50][CH:49]=[CH:48][C:44]=3[C:45]([OH:47])=[O:46])[N:42]=2)[CH:26]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)HCID 72312724[2-(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester

Product 1

HCID 1363892882-(3-{(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro[1,2,4]triazol-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To 2 ml of a DMF solution containing 130 mg of [2-(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester (Example (21h)), 46 mg of 2-hydrazinobenzoic acid hydrochloride and 0.200 ml of triethylamine were added. The resulting mixture was stirred at 80° C. for 8 hours under a nitrogen atmosphere, and then the reaction mixture was concentrated. The residue was dissolved in 3 ml of methanol and 0.3 ml of acetic acid, and 250 mg of sodium cyanotrihydroborate was added thereto. The mixture was stirred at room temperature overnight. To this reaction mixture, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate) to give 2-(3-{(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro[1,2,4]triazol-1-yl)benzoic acid.

Workup

  1. additionwere added
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in 3 ml of methanol
  4. addition0.3 ml of acetic acid, and 250 mg of sodium cyanotrihydroborate was added
  5. stirringThe mixture was stirred at room temperature overnight
  6. additionTo this reaction mixture, water was added
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customThe desiccating agent was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate)

Sources & evidence

ORD record
ord-2786987d61d14f7088be4329ae51965f
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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